Two cyanoethylene-based fluorescence probes for highly efficient cyanide detection and practical applications in drinking water and living cells

Abstract

Cyanide detection methods are urgently needed due to the highly lethal to human beings. Herein, we report two fluorescence probes (Probe 1 and Probe 2) based on cyanoethylene group for cyanide anion (CN^-) detection. The selective recognition for CN^- was confirmed by the completely opposite green fluorescence of Probe 1 and red fluorescence of Probe 2 observed by fluorescence spectra and naked eyes. The probes take advantages of the large Stokes shift (~160 nm), rapid response (30 s), anti-interference performance and low detection limit (Probe 1: 12.4 nM, Probe 2: 101 nM). The sensing mechanism is certificated to the nucleophilic attack of CN^- to electron-deficient cyanoethylene group of probes, which was demonstrated by ¹H NMR titration, HR-MS, Job's plot and IR spectroscopy. Density functional theory (DFT) calculations were carried out to analyze the mechanism in theory. Further, practical applications were studied. Easy-to-use test strips treated with Probe 1 or Probe 2 are capable of CN^- detection in pure drinking water. The good biocompatibility and membrane penetrability have achieved the bioimaging capability of Probe 1 and Probe 2 in living HepG-2 cells, making the probes promising for use in real lives.

Keywords: Cell imaging; Cyanide detection; Cyanoethylene; DFT; Fluorescence probe.